Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → HCID 13206552, compound

HRID 1980445Notes

Reaction equation

HRID 1980445 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([N:28]=[C:29]=[O:30])(=[O:27])=[O:26])=[O:18]>C(#N)C>[CH3:13][N:12]([CH3:14])[C:10]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[N:3]=[C:2]([NH:1][C:29]([NH:28][S:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:17]([O:16][CH3:15])=[O:18])(=[O:27])=[O:26])=[O:30])[N:11]=1

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 20401649HCID 20401649, compound

Product 1

HCID 13206552HCID 13206552, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.3 g (0.0068 mol) of 2-amino-4-dimethylaminopteridine and 1.7 g of 2-methoxycarbonylphenylsulfonyl isocyanate in 40 ml of acetonitrile was refluxed for 4 hours and the hot mixture was vacuum filtered to obtain 2.5 g (85% of theory) of N-(4-dimethylaminopteridin-2-yl)-N'-(2-methoxycarbonylphenylsulfonyl)-urea in the form of brownish crystals melting at 219° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-3c23317524d94ab2a7c0361ac1ff1a92
Source dataset
uspto-grants-1985_04
Patent number
US04509972

Reaction notes

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